Our invention relates to 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives wherein the 1-oxo-substitued and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR9## wherein Y.sub.1 represents one of the moieties: ##STR10## and wherein one of the bicyclopentadiene derivatives is represented by the structure: ##STR11## wherein Z.sub.1 and Z.sub.2 are the same or different C.sub.1 -C.sub.3 lower alkyl, C.sub.2 -C.sub.3 acyl or hydrogen and Z.sub.3 represents methyl or hydrogen with the provisio that Z.sub.1 and Z.sub.2 are not both hydrogen.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting, intense, substantive green, woody, privet hedge-like (Ligustrum vulgare)-like, floral, lilac, ozoney, phenyl and anisic aromas with fruity, fresh green, ozoney, fresh air, "ocean breeze", and anisic topnotes are highly desirable in several types of perfume compositions, perfumed articles and colognes (e.g., fruity and floral fragrances).
Perfume uses of ethoxy benzene derivatives are well known in the literature. Thus, Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume I, published in 1969 by the author at Monograph No. 713 discloses the compound having the structure: ##STR12## for use in perfumery. Arctander discloses that the compound having the structure: ##STR13## has a powerful, pungent-floral, deep-sweet, warm odor suggestive of Ylang-Ylang, Pandanus and other exotic flowers. Arctander indicates that this compound is useful in perfume compositions of the heavy-floral type, in artificial Ylang-Ylang, and in various types of soap perfumes and in general as a floralizer with considerable power. Arctander further states that the compound having the structure: ##STR14## has a "peculiar nut-like, or earthy undertone". Bielstein E, II, 6, 488, H6, System 530a, 522-523 (abstract of Le Brazidec, Bull.Soc.Chim.France[4], 31 263) discloses that the compound having the structure: ##STR15## has an anisic aroma. The synthesis of this compound is disclosed by Le Brazidec and is further disclosed by Dutton, et al, Canadian Journal of Chemistry, 31 (1953), 1138, 1140. The structure: ##STR16## wherein R is methyl is shown by Bielstein, Volume E, IV6, at page 3288 and is also disclosed at Chem. Abstracts, Volume 47, No. 2716h (abstract of J.Elisha Mitchell Sci.Soc., Volume 66, 171-4 (1950). The compound having the structure: ##STR17## is also disclosed in Schoot, et al, U.S. Pat. No. 2,996,514.
The compounds having the structures: ##STR18## are indicated to be prepared by Chem. Abstracts, Volume 73, 1970, 66192c. The preparation of the compound: ##STR19## is also shown to be prepared by Bielstein, E IV 6, at page 3280, Chem. Abstracts, 1961, 13386d (Zavgorodnii II) and Chem.Abstracts Volume 49, (1955) No. 8848z (Zavgorodnii I).
Furthermore, the compound having the structure: ##STR20## is shown to be prepared by Zavgorodnii III at Chem.Abstracts Volume 71 (1969) No. 3088m. The compound having the structure: ##STR21## is shown to be prepared using the compound having the structure: ##STR22## as a starting material according to the reaction: ##STR23## by Bielstein E III 6, H6, 548. The compound having the structure: ##STR24## is shown to be prepared using as a starting material the compound having the structure: ##STR25## according to the reaction: ##STR26## by Bielstein E IV 6, page 3378 and by Dutton, et al, Canadian Journal of Chemistry 31 (1953) pages 1138, 1142.
The compound having the structure: ##STR27## is shown to be prepared by Bielstein E III 6, H6, 505-6 System No. 530, abstract of Ipatieff, et al, Journal of American Soc. 60 (1938) 1161 and Bert, Bull.Soc.Chim. 37, 1252-70 (1925).
For use in perfumery, compounds having the structures: ##STR28## where Z.sub.3 is hydrogen is disclosed in the International Flavors & Fragrances Inc. "Fragrance Ingredient Specification Compendium" published by International Flavors & Fragrances Inc. at pages 19, 20 and 72 and in the International Flavors & Fragrances Inc. "Perfumers Compendium" at pages 9 and 36.
Nothing in the prior art, however, discloses the unexpected, unobvious and advantageous organoleptic properties of the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxybenzenes and mixtures thereof with bicyclopentadiene derivatives of our invention.